CA2420341A1 - Compositions adapted for chain linking - Google Patents

Compositions adapted for chain linking Download PDF

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Publication number
CA2420341A1
CA2420341A1 CA002420341A CA2420341A CA2420341A1 CA 2420341 A1 CA2420341 A1 CA 2420341A1 CA 002420341 A CA002420341 A CA 002420341A CA 2420341 A CA2420341 A CA 2420341A CA 2420341 A1 CA2420341 A1 CA 2420341A1
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Prior art keywords
polymer
linking
chain
composition
hereinbefore defined
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CA002420341A
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CA2420341C (en
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Patrick Terence Mcgrail
Jeffrey Thomas Carter
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Cytec Technology Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/20—Polysulfones
    • C08G75/23—Polyethersulfones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/06—Polysulfones; Polyethersulfones

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Reinforced Plastic Materials (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Lubricants (AREA)
  • Graft Or Block Polymers (AREA)
  • Fertilizers (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

A polymer composition comprising chains of at least one aromatic polymer or a mixture thereof together with at least one chain linking component wherein the at least one aromatic polymer comprises polymer chains of number average molecular weight (Mn) in a first range and characterised by a polymer flow temperature, and having at least one reactive end group, and wherein the at least one chain linking component comprises at least two linking sites, characterised in that a plurality of the polymer chain end groups are adapted to react with the linking sites at chain linking temperature in excess of the polymer flow temperature to form linked polymer chains of number average molecular weight (Mn) in a second range which is in excess of the first range, substantially thermoplastic in nature; process for the preparation thereof;
prepreg, composite or shaped product obtained therewith and the use thereof.

Claims (36)

1. A polymer composition comprising chains of at least one aromatic polymer or a mixture thereof together with at least one chain linking component wherein the at least one aromatic polymer comprises polymer chains of number average molecular weight (Mn) in a first range and characterised by a polymer flow temperature, and having at least one reactive end group, and wherein the at least one chain linking component comprises at least two linking sites, characterised in that a plurality of the polymer chain end groups are adapted to react with the linking sites at chain linking temperature in excess of the polymer flow temperature to form linked polymer chains of number average molecular weight (Mn) in a second range which is in excess of the first range, substantially thermoplastic in nature.
2. A polymer composition as claimed in Claim 1 in the form of a precursor composition comprising an amount of at least one aromatic polymer as hereinbefore defined, together with an amount thereof, which has been prereacted at chain terminating conditions with the at least one chain linking component as hereinbefore defined to form polymer chains of Mn in the first range, characterised by a polymer flow temperature and having its reactive end groups terminated with linking component, characterised in that a plurality of the polymer chain reactive end groups are adapted to react with the linking sites of linking component terminated polymer chains at chain linking temperature in excess of the polymer flow temperature to form linked polymer chains of number average molecular weight (Mn) in a second range which is in excess of the first range.
3. A polymer composition as claimed in any of Claims 1 & 2 wherein flow temperature is the temperature at which the polymer attains a suitably molten or fluid state to enable a degree of polymer chain mobility to orient or align itself for reaction.
4. A polymer composition as claimed in any of Claims 1 to 3 wherein the chain linking temperature is higher than a product processing temperature, to remove solvent and improve wet out of the prepreg.
5. A polymer composition as claimed in any of Claims 1 to 4 wherein the number average molecular weight of the polyaromatic in the second range is in the range 9000 to 60000, for example 11000 to 25000, and in the first range is in the range of 2000 to 11000, for example in the range of 3000 to 9000.
6. A polymer composition as claimed in any of Claims 1 to 5 which comprises a first and second polymers having the same polymer backbone but different end groups, both being amorphous; or comprises a first aromatic polymer having a lower flow temperature than a second similar aromatic polymer, both being amorphous the second polymer being rendered in flowable form in the presence of the first polymer in fluid form, thereby providing a processing aid; or comprises an amorphous polymer and a crystalline or semi crystalline polymer having a characteristic melting point, the semi crystalline polymer being rendered flowable by solvent effect of the first polymer, acting as a cosolvent, diluent, dispersant, carrier or the like for the second aromatic polymer.
7. A polymer composition as claimed in any of Claims 1 to 6 wherein Reactive end groups (Y) and chain linking sites (Z) are selected from any functional groups providing active hydrogen and any polar functional group adapted to react at elevated temperature in the presence of an electrophile, preferably selected from active H, OH, NH2, NHR or SH wherein R is a hydrocarbon group containing up to 8 carbon atoms, epoxy, (meth)acrylate, iso)cyanate, isocyanate ester, acetylene or ethylene as in vinyl or allyl, maleimide, anhydride, carboxylic acid, oxazoline and monomers containing unsaturation; preferably reactive end groups Y are selected from active H, OH, NH2, NHR or SH and chain linking sites Z are selected from epoxy, (meth)acrylate, (iso)cyanate, isocyanate ester, acetylene or ethylene as in vinyl or allyl, maleimide, anhydride, carboxylic acid, oxazoline and monomers containing unsaturation.
8. A polymer composition as claimed in any of Claims 1 to 7 wherein a chain linking component is of the formula B(Z)n(Z')n' wherein B is a polymer chain or is a carbon atom backbone having from 1 to 10 carbon atoms, more preferably is an oligomer or polymer or is an aliphatic, alicyclic or aromatic hydrocarbon optionally substituted and/or including heteroatoms N,S,O or is a single bond or nucleus such as C, O, S, N or Transition metal;

Z and Z' are each independently selected from functional groups as hereinbefore defined for Z;

n and n' are each zero or a whole number integer selected from 1 to 6; and the sum of n and n' is at least 2, preferably 2 to 10,000, more preferably 2 to 10 or 10 to 500 or 500 to 10000.
9. A polymer composition as claimed in any of Claims 1 to 8 wherein a chain linking component comprises a compound of formula B(Z)n wherein B and Z are as hereinbefore defined in Claim 8 and n is selected from 2 to 6.
10. A polymer composition as claimed in and of Claims 1 to 9 wherein a linear or branched polymer chain having at least two ends comprises at least two reactive end groups and comprises a diol, polyol, diamine, polyamine, dithiol or polythiol or the like and a chain linking component comprises at least two linking sites whereby at least two polymer chains may be linked together, and comprises a diepoxy, polyepoxy, di(meth)acrylate, poly(meth)acrylate, di(iso)cyanate, poly(iso)cyanate, diacetylene, polyacetylene, dianhydride, polyanhydride, dioxazoline, polyoxazoline.
11. A polymer composition as claimed in any of Claims 1 to 10 wherein linking components are selected from the structures:

Epikote 28 [O(CH2CH)CH2OPh]2C(CH3)2 Benzophenone tetra carboxylic acid dianhydride (BTDA) [O(CO)2Ph]2CO Maleic anhydride having units -[CHC(O)OC(O)CH]-
12. A polymer composition as claimed in any of Claims 1 to 11 wherein a polymer chain reactive end group is hydroxy and corresponds to a linking site functionality which is epoxy, whereby reaction thereof produces a .beta.
hydroxy ether linkage in polymers of increased number average molecular weight having either hydroxy or epoxy end groups as desired; or the reactive end group is and the linking site functionality is anhydride, whereby reaction thereof produces an imide linkage in polymers of increased number average molecular weight having NH2 or anhydride end groups; or the reactive end group is NH2 and the linking site functionality is maleimide.
13. A polymer composition as claimed in any of Claims 1 to 12 wherein the reactive end groups and linking sites are present, calculated by the amount of polymer chain and linking component, in the required stoichiometric amounts to enable up to 100% linking of polymer chains in multiples of two (binary linking), three (tertiary linking), four (ternary linking), for example in a "star"
architecture, and combinations thereof.
14. A polymer composition as claimed in any of Claims 1 to 13 wherein an amount of additional intra or inter chain functionality is provided in the form of functional groups along the chain length whereby the chain linking component is selected to provide such functionality, selected from solvent resistance (F), cross-linking grafting sites (unsaturated groups), Tg enhancing or compatibilising agents eg a microstructure compatible and reactive with another polymer.
15. A polymer composition as claimed in any of Claims 1 to 14 wherein the at least one polyaromatic comprises ether-linked and/or thioether-linked repeating units, the units being selected from the group consisting of -(PhAPh)n-and optionally additionally -(Ph)a-wherein A is SO2 or CO, Ph is phenylene, n= 1 to 2, a = 1 to 4 and when a exceeds 1, said phenylenes are linked linearly through a single chemical bond or a divalent group other than -A- or are fused together directly or via a cyclic moiety such as a cycloalkyl group, a (hetero) aromatic group, or cyclic ketone, amide, amine, or imine, said at least one polyarylsulphone having reactive pendant and/or end groups.
16. A polymer composition as claimed in any of Claims 1 to 15 wherein the at least one polyaromatic comprises at least one polyaryl sulphone comprising ether-linked repeating units, optionally additionally comprising thioether-linked repeating units, the units being selected from the group consisting of -(PhSO2Ph)n-and optionally additionally -(Ph)a-wherein Ph is phenylene, n= 1 to 2, a = 1 to 3 and when a exceeds 1, said phenylenes are linked linearly through a single chemical bond or a divalent group other than -SO2- or are fused together, provided that the repeating unit -(PhSO2Ph)n- is always present in said at least one polyarylsulphone in such a proportion that on average at least two of said units -(PhSO2Ph)n- are in sequence in each polymer chain present, said at least one polyarylsulphone having reactive pendant and/or end groups.
17. A polymer composition as claimed in any of Claims 1 to 16 wherein the polyaromatic comprises polyether sulphone, more preferably a combination of polyether sulphone and polyether ether sulphone linked repeating units, in which the phenylene group is meta- or para- and is preferably para and wherein the phenylenes are linked linearly through a single chemical bond or a divalent group other than sulphone, or are fused together.
18. A polymer composition as claimed in Claims 16 and 17 wherein the units are:

I X Ph SO2 Ph X Ph SO2 Ph ("PES") and II X (Ph)a X Ph SO2 Ph ("PEES") where X is O or S and may differ from unit to unit; the ratio is I to II
(respectively) preferably between 10:90 and 80:20 such as between 35:65 and 65:35.
19. A polymer composition as claimed in Claims 16 to 18 wherein relative proportions of the repeating units of the polyarylsulphone expressed in terms of the weight percent SO2 content, defined as 100 times (weight of SO2)/(weight of average repeat unit) is at least 22, preferably 23 to 25%. When a = 1 this corresponds to PES/PEES ratio of at least 20:80, preferably in the range 35:65 to 65:35.
20. A polymer composition as claimed in Claims 1 to 19 additionally comprising a thermoset polymer component selected from the group consisting of an epoxy resin, an addition-polymerisation resin, especially a bis-maleimide resin, a formaldehyde condensate resin, especially a formaldehyde-phenol resin, a cyanate resin, an isocyanate resin, a phenolic resin and mixtures of two or more thereof.
21. A polymer composition as claimed in Claim 20 wherein the weight proportion of thermoplast component in the composition is typically in the range 5 to 100%, preferably 5 to 90%, especially 5 to 50, for example 5 to 40%.
22. A process for the preparation of a polymer composition comprising at least one aromatic polymer or a mixture thereof, the process comprising:

i) providing polyaromatic polymer chains having Mn in a first range as hereinbefore defined and characterised by a polymer flow temperature, wherein the at least one polyaromatic polymer chains have at least one reactive end group, and ii) providing at least one chain linking component having at least two linking sites as hereinbefore defined, and iii) admixing at a first temperature which is less than the chain linking temperature at which the reactive end group and linking sites are adapted to react as hereinbefore defined.
23. A process as claimed in Claim 22 wherein admixing is carried out at or below the composition flow temperature employed for shaping the composition, and shaping is carried out simultaneously or subsequently.
24. A process as claimed in any of Claims 22 and 23 wherein the polymers are prepared from monomers obtained and isolated with the use of first and second fluids in the substantial absence of an effective amount of azeotrope.
25. A process as claimed in Claim 24 wherein the monomers are prepared in a preselected Mn and as the monomers are in solution introducing alternative end groups by reaction in the solution prior to isolation thereof.
26. A process as claimed in Claim 24 or 25 wherein first fluid comprises at least one dipolar aprotic solvent, optionally present in a fluid mixture with other liquids or non liquids, which acts to promote the polymerisation reaction, preferably selected from one or more of sulphur oxides, such as sulphoxides and sulphones, formamides, pyrrolidones, cyclic ketones and the like, and the second fluid is selected from alcohols and demineralised water or demineralised aqueous solvents and mixtures thereof.
27. A process as claimed in any of Claims 24 to 26 wherein the polymer is as Claimed in Claims 16 to 19, wherein monomer precursors are selected according to the desired polymer composition comprising polyethersulphones to polyetherethersulphones in a desired ratio employing respective proportions of bisphenol and dihalides to monophenol in the same molar amounts in the range of 10:90-100:0, preferably 10:90-70:30.
28. A process as claimed in any of Claims 24 to 27 wherein reactive end groups are introduced at the outset with the monomer polymer precursors.
29. A process as claimed in any of Claims 24 to 28 wherein end groups comprising halo or hydroxy reactive groups are obtained by addition of an excess of a component as hereinbefore defined in Claim 27 providing the repeating units of the polyarylsulphone, for example in the form of a dihalide or a bisphenol and monophenol; alternatively end groups comprising amino reactive groups may be obtained by addition of a pre-determined amount of a monomer, which does not provide repeating units of the polyarylsulphone, for example of aminophenol.
30. A process for providing a composition as hereinbefore defined in any of Claims 1 to 21, as a shaped article or film, such as impregnated, moulded, injection moulded, extruded or the like articles or cast, sprayed or rollered films, comprising obtaining the composition according to the invention as hereinbefore defined, subjecting to a first temperature as hereinbefore defined corresponding to the flow temperature of the unreacted composition and shaping according to known techniques, optionally in solution of a suitable solvent, subjecting to a second elevated temperature as hereinbefore defined corresponding to the temperature for chain linking reaction of the composition and obtaining a shaped article or film having increased number average molecular weight in a second range as hereinbefore defined.
31. A process as claimed in Claim 30 wherein processing conditions comprise elevated temperature in the range of 150-400°C more preferably 300°C, for example 190-250°C.
32. A resin composition as claimed in any of Claims 1 to 21 for fabrication of structures, including load-bearing or impact resisting structures, containing a reinforcing agent such as fibres.
33. A prepreg comprising a composition as hereinbefore defined in any of Claims 1 to 21 and continuous fibres, obtained by a process as hereinbefore defined.
34. A composite comprising a pre-preg as hereinbefore defined in Claim 33 laminated together by heat and pressure, for example by autoclave, compression moulding, or by heated rollers, at a temperature above the curing temperature of the polymer composition.
35. A thermoplast or a thermoplast-modified thermoset resin shaped product comprising a composition, pre-preg, laminar composite or shaped product as hereinbefore defined in any of Claims 1 to 21, 33 to 35 and, which is obtained by the method as hereinbefore defined in Claim 30 or 31, for use in transport such as aerospace, aeronautical, marine or automotive industries, rail and coach industries or in building/construction industry, or for use in non-high performance transport applications, non-construction applications and adhesive applications, including high temperature adhesive applications.
36. A composition, pre-preg, laminar composite or shaped product as hereinbefore described or illustrated in the description and figures.
CA2420341A 2000-08-22 2001-08-20 Compositions adapted for chain linking Expired - Lifetime CA2420341C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0020620.1 2000-08-22
GBGB0020620.1A GB0020620D0 (en) 2000-08-22 2000-08-22 Compostions adapted for chain linking
PCT/GB2001/003729 WO2002016456A2 (en) 2000-08-22 2001-08-20 Compositions adapted for chain linking

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CA2420341A1 true CA2420341A1 (en) 2002-02-28
CA2420341C CA2420341C (en) 2011-04-05

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JP (1) JP5081364B2 (en)
KR (1) KR100849280B1 (en)
CN (1) CN1250606C (en)
AT (1) ATE316109T1 (en)
AU (2) AU7996301A (en)
BR (1) BR0113433A (en)
CA (1) CA2420341C (en)
DE (1) DE60116777T2 (en)
DK (1) DK1311570T3 (en)
ES (1) ES2257426T3 (en)
GB (1) GB0020620D0 (en)
IL (2) IL154399A0 (en)
MX (1) MXPA03001411A (en)
MY (1) MY123932A (en)
NO (1) NO20030758L (en)
RU (1) RU2278126C2 (en)
WO (1) WO2002016456A2 (en)
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KR100849280B1 (en) 2008-07-29
MXPA03001411A (en) 2003-08-29
NO20030758L (en) 2003-04-08
CA2420341C (en) 2011-04-05
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CN1250606C (en) 2006-04-12
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